Departure months
Trip length
Search
P&O Cruises

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Fort-de-France, Basseterre, Saint Kitts & Philipsburg

Dec 18, 2026 → Jan 1, 2027 • Bridgetown ↔

$541 above typical

From $3,107

$222/night

Priced high

↑21% above typical

Norwegian Cruise Line

Norwegian Viva • Norwegian Cruise Line

7-night Southern Caribbean Loop via Basseterre, Saint Kitts & Castries

Jan 23, 2028 → Jan 30, 2028 • San Juan ↔

$185 above typical ↘ Trending down

From $1,064

$152/night

Priced high

↑21% above typical

P&O Cruises

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Dec 25, 2027 → Jan 8, 2028 • Bridgetown ↔

$473 above typical

From $2,742

$196/night

Priced high

↑21% above typical

Princess Cruises

Emerald Princess • Princess Cruises

5-night Eastern Caribbean Arc via Saint Thomas & Philipsburg

Nov 21, 2027 → Nov 26, 2027 • San Juan → Bridgetown

$126 above typical

From $744

$149/night

Priced high

↑20% above typical

P&O Cruises

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Nov 13, 2027 → Nov 27, 2027 • Bridgetown ↔

$362 above typical

From $2,161

$154/night

Priced high

↑20% above typical

P&O Cruises

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Nov 26, 2027 → Dec 10, 2027 • Bridgetown ↔

$362 above typical

From $2,161

$154/night

Priced high

↑20% above typical

Holland America

Rotterdam • Holland America

21-night Western Caribbean Loop via Half Moon Cay, Falmouth & Cozumel

Dec 12, 2026 → Jan 2, 2027 • Fort Lauderdale ↔

$460 above typical

From $2,799

$133/night

Priced high

↑20% above typical

P&O Cruises

Britannia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts

Feb 5, 2027 → Feb 19, 2027 • Bridgetown ↔

$443 above typical

From $2,742

$196/night

Priced high

↑19% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown

Jan 10, 2027 → Jan 17, 2027 • San Juan ↔

$240 above typical

From $1,499

$214/night

Priced high

↑19% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown

Jan 24, 2027 → Jan 31, 2027 • San Juan ↔

$240 above typical

From $1,499

$214/night

Priced high

↑19% above typical

Princess Cruises

Crown Princess • Princess Cruises

7-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Saint George's

Jan 17, 2027 → Jan 24, 2027 • San Juan ↔

$154 above typical

From $969

$138/night

Priced high

↑19% above typical

P&O Cruises

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Nov 12, 2027 → Nov 26, 2027 • Bridgetown ↔

$335 above typical

From $2,134

$152/night

Priced high

↑19% above typical

MSC Cruises

MSC Seaview • MSC Cruises

7-night Southern Caribbean Loop via Pointe-à-Pitre, Castries & Bridgetown

Feb 20, 2027 → Feb 27, 2027 • Fort-de-France ↔

Great balance

From $1,204

$172/night

Princess Cruises

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg

Mar 5, 2027 → Mar 12, 2027 • Bridgetown ↔

$181 above typical

From $1,194

$171/night

Priced high

↑18% above typical

P&O Cruises

Britannia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts

Nov 13, 2026 → Nov 27, 2026 • Bridgetown ↔

$311 above typical

From $2,134

$152/night

Priced high

↑17% above typical

Princess Cruises

Emerald Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Nov 21, 2027 → Nov 28, 2027 • San Juan ↔

$137 above typical

From $1,002

$143/night

Priced high

↑16% above typical

Royal Caribbean International

Grandeur of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

May 29, 2027 → Jun 5, 2027 • San Juan ↔

$125 above typical

From $942

$135/night

Priced high

↑15% above typical

Virgin Voyages

Valiant Lady • Virgin Voyages

7-night Southern Caribbean Loop via Philipsburg, Bridgetown & Castries

Jan 16, 2027 → Jan 23, 2027 • San Juan ↔

$140 above typical

From $1,113

$159/night

Priced high

↑14% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown

Feb 21, 2027 → Feb 28, 2027 • San Juan ↔

$180 above typical

From $1,439

$206/night

Priced high

↑14% above typical

P&O Cruises

Britannia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts

Feb 6, 2027 → Feb 20, 2027 • Bridgetown ↔

$308 above typical

From $2,607

$186/night

Priced high

↑13% above typical

Filters

Filters

Reset
Deal Signals
Trip Style
Cabin Type
Ports Visited
Cruise Line & Ship
Price

Per person